ethyl 3-[N-(4-methylbenzenesulfonyl)]aminobenzoate | 349620-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-[N-(4-methylbenzenesulfonyl)]aminobenzoate
• 英文别名: ethyl 3-(4-methylphenylsulfonamido)benzoate；Ethyl 3-[(4-methylphenyl)sulfonylamino]benzoate
• CAS: 349620-90-2
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: UANRYPIPXHOUQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[N-(4-methylbenzenesulfonyl)]aminobenzoate 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 氧气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 ethyl 3-(3-cyclohexyl-2-methyl-2-(p-tolyl)propanamido)benzoate
  参考文献：
  名称：

  酮基二氢喹唑啉酮对共轭烯烃的可见光光催化双碳官能化

  摘要：

  描述了N- (芳基磺酰基)丙烯酰胺与酮基二氢喹唑啉酮的可见光光催化 1,2-芳基烷基化。脂肪酮的正式C-C键裂解与串联自由基烷基化/1,4-芳基迁移/脱磺酰化结合形成两种不同类型的邻位C-C键并构建全碳季α-立体中心，从而增强carbogenic 复杂性和容忍不同的功能。除了伸缩合成和产品多样化之外，该方法的特点是在环境温度下利用氧作为绿色氧化剂，使用亲核烷基自由基前体（二氢喹唑啉酮）对共轭N- (芳基磺酰基) 丙烯酰胺进行自由基双碳官能化。

  DOI：

  10.1021/acs.orglett.3c00175
• 作为产物：
  描述：

  3-羟基苯甲酸乙酯 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 2-甲基-2-丁醇 、 乙腈 为溶剂， 反应 16.0h， 生成 ethyl 3-[N-(4-methylbenzenesulfonyl)]aminobenzoate
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u

文献信息

• Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: <i>N</i> , or <i>O</i> ‐Difluoromethylation, <i>N</i> ‐Ethylation and <i>S</i> ‐(ethoxycarbonyl)difluoromethylation
  作者：Arghya Polley、Gurupada Bairy、Pritha Das、Ranjan Jana

  DOI：10.1002/adsc.201800824

  日期：2018.11.5

  chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl‐protected aniline

  在这份报告中，我们探索了溴二氟乙酸乙酯的化学反应的三重模式。通常，溴二氟乙酸已被用作软亲核试剂的二氟甲基化的二氟卡宾前体。在这里，我们已经公开了溴二氟乙酸乙酯的亲核性和碱依赖性发散化学反应性。它提供了氢氧化锂和碳酸铯，分别促进了甲苯磺酰基保护的苯胺和缺电子的酚的二氟甲基化作用。有趣的是，将碱从氢氧化锂转变为4- N，N-二甲基氨基吡啶（DMAP）甲苯磺酰基保护的苯胺，得到了相应的N-乙基化产物。而高度亲核的苯硫酚提供了相应的S羰基乙氧基二氟甲基化产物在酯水解之前通过快速的S N 2攻击溴原子而形成。这种机制差异是通过几个控制实验确定的。结果表明，二氟甲基化反应是通过串联原位酯水解/脱羧-脱溴化二氟卡宾的形成并随后被软亲核试剂-NHTs或电子缺陷型酚-OH基团捕获而进行的。在DMAP的存在下，酯的水解受到干扰，相反，在乙基部分的亲核攻击提供了N-乙基化产物。因此，除了开发实用的碱促氮素胺和电
• LRRK2 GTP BINDING INHIBITORS FOR TREATMENT OF PARKINSON'S DISEASE AND NEUROINFLAMMATORY DISORDERS
  申请人：University of Maryland, Baltimore

  公开号：US20150361038A1

  公开（公告）日：2015-12-17

  Compounds, and methods of using the same, are provided as therapies for the treatment leucine-rich repeat kinase-2 (LRRK2)-related disorders including, but not limited to, neurodegenerative and neuroinflammatory disorders, such as Parkinson's Disease.

  提供了化合物及其使用方法，作为治疗与白氨酸富含重复激酶-2（LRRK2）相关的疾病的疗法，包括但不限于神经退行性和神经炎症性疾病，如帕金森病。
• US9701627B2
  申请人：——

  公开号：US9701627B2

  公开（公告）日：2017-07-11
• A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates
  作者：Shashank Shekhar、Travis B. Dunn、Brian J. Kotecki、Donna K. Montavon、Steven C. Cullen

  DOI：10.1021/jo200443u

  日期：2011.6.3

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.
• Visible-Light-Photocatalyzed Dicarbofunctionalization of Conjugated Alkenes with Ketone-Based Dihydroquinazolinones
  作者：Pinku Prasad Mondal、Subham Das、Sreelakshmi Venugopalan、Malavika Krishnan、Basudev Sahoo

  DOI：10.1021/acs.orglett.3c00175

  日期：2023.3.10

  α-stereocenter, thus enhancing the carbogenic complexity and tolerating diverse functionalities. Additional to telescopic synthesis and product diversification, this method features a radical dicarbofunctionalization of conjugated N-(arylsulfonyl)acrylamides with a nucleophilic alkyl radical precursor (dihydroquinazolinone) utilizing oxygen as a green oxidant at ambient temperature.

  描述了N- (芳基磺酰基)丙烯酰胺与酮基二氢喹唑啉酮的可见光光催化 1,2-芳基烷基化。脂肪酮的正式C-C键裂解与串联自由基烷基化/1,4-芳基迁移/脱磺酰化结合形成两种不同类型的邻位C-C键并构建全碳季α-立体中心，从而增强carbogenic 复杂性和容忍不同的功能。除了伸缩合成和产品多样化之外，该方法的特点是在环境温度下利用氧作为绿色氧化剂，使用亲核烷基自由基前体（二氢喹唑啉酮）对共轭N- (芳基磺酰基) 丙烯酰胺进行自由基双碳官能化。